| Red Sweater | | 1931 | | | Honorable Mention |
| Red Tulip | | 1936 | | | |
| Red Tulips | | 1936 | | | |
| Red, white and blue | | 1932 | | | |
| Reflection | | 1934 | | | |
| Reflection of a Broken Doll | | 1930 | | | |
| Reflections | | 1934 | | | |
| Reflections | | 1930 | | | |
| Reflections | | 1938 | | | |
| Reflections and Shadows | | 1930 | | | |
| Reflections, Canaan, Connecticut | | 1923 | | | |
| Refugees | | 1939 | | | |
| Refugees | | 1939 | | | Honorable Mention |
| Registered Distillery | | 1936 | | | |
| Reheating Steel Ingots | | 1933 | | | |
| Relations | | 1936 | | | Special Award |
| Relief of Dr. Thwing | | 1926 | | | |
| Reminiscence | | 1922 | | | |
| Renaissance and Gothic, Chartres | | 1927 | | | |
| Renovized--1932 | | 1933 | | | Third Prize |
| Repairing Boat, Provincetown, Massachusetts | | 1919 | | | |
| Repose | | 1934 | | | Third Prize |
| Republic Steel | | 1936 | | | |
| Rest | | 1935 | | | |
| Resting | | 1922 | | | |
| Resting | | 1937 | | | |
| Resting in the Fields | | 1928 | | | |
| Resting River Bug | | 1939 | | | |
| Rhythm | | 1934 | | | |
| Rhythm | | 1933 | | | |
| Rhythm | | 1937 | | | |
| Rhythmic Hills | | 1929 | | | |
| Rhythmic tanks | | 1939 | | | |
| Rice Planter | | 1937 | | | |
| Rift in the Mountain | | 1931 | | | |
| Rippling Waters | | 1919 | | | |
| Rising Cantilevers | | 1929 | | | Second Prize |
| River at Chicopee, Mass. | | 1923 | | | |
| River at Pittsburgh | | 1922 | | | |
| River Bank | | 1927 | | | |
| River Ferry | | 1934 | | | |
| River from Pittsburgh | | 1932 | | | |
| River Patterns | | 1931 | | | |
| River Road | | 1929 | | | |
| River Scene | | 1932 | | | |
| River Scene | | 1939 | | | |
| River Traffic | | 1922 | | | |
| River Traffic | | 1939 | | | |
| River Traffic | | 1930 | | | Second Prize, Landscape and Miscellaneous |
| River Valley, West Virginia | | 1938 | | | |
